JP2909224B2 - イブプロフエン及びそのアルキルエステルの製造法 - Google Patents

イブプロフエン及びそのアルキルエステルの製造法

Info

Publication number: JP2909224B2
Authority: JP; Japan
Prior art keywords: isobutylphenyl; palladium; ethane; halo; carbon monoxide
Prior art date: 1989-12-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP2410576A

Other languages

English (en)

Japanese (ja)

Other versions

JPH03279345A (ja

Inventor

バーバラ・クラツク・スタリイ

ロニイ・ウエン−ロング・リン

エルドン・アール・アトキンソン・ジユニア

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ARUBEMAARU CORP

Original Assignee

ARUBEMAARU CORP

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-12-18

Filing date

1990-12-14

Publication date

1999-06-23

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23792726&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP2909224(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-12-14 Application filed by ARUBEMAARU CORP filed Critical ARUBEMAARU CORP

1991-12-10 Publication of JPH03279345A publication Critical patent/JPH03279345A/ja

1999-06-23 Application granted granted Critical

1999-06-23 Publication of JP2909224B2 publication Critical patent/JP2909224B2/ja

2014-06-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims description 21
229960001680 ibuprofen Drugs 0.000 title claims description 19
238000000034 method Methods 0.000 title description 32
125000005907 alkyl ester group Chemical group 0.000 title 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
229910002091 carbon monoxide Inorganic materials 0.000 claims description 20
239000003446 ligand Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
-1 aliphatic alcohols Chemical class 0.000 claims description 16
229910052763 palladium Inorganic materials 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 13
150000002941 palladium compounds Chemical class 0.000 claims description 6
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
235000019441 ethanol Nutrition 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
238000005810 carbonylation reaction Methods 0.000 description 11
230000006315 carbonylation Effects 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
101150003085 Pdcl gene Proteins 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
SPBVCQUMYJRBMD-UHFFFAOYSA-N 1-(1-chloroethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C(C)Cl)C=C1 SPBVCQUMYJRBMD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
VTMSSJKVUVVWNJ-UHFFFAOYSA-N 1-ethenyl-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C=C)C=C1 VTMSSJKVUVVWNJ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
239000004912 1,5-cyclooctadiene Substances 0.000 description 1
WHSROYYJBJDRBV-UHFFFAOYSA-N 1-(1-bromoethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C(C)Br)C=C1 WHSROYYJBJDRBV-UHFFFAOYSA-N 0.000 description 1
ZBIVAPCIGWNIEH-UHFFFAOYSA-N 1-(2-methylpropyl)-4-[1-[4-(2-methylpropyl)phenyl]ethyl]benzene Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C1=CC=C(CC(C)C)C=C1 ZBIVAPCIGWNIEH-UHFFFAOYSA-N 0.000 description 1
VLVILBSSXMZZCB-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanol Chemical compound CC(C)CC1=CC=C(C(C)O)C=C1 VLVILBSSXMZZCB-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical class CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
XMRHRPOYXVMEEP-UHFFFAOYSA-N 1-ethyl-2-(2-methylpropyl)benzene Chemical compound CCC1=CC=CC=C1CC(C)C XMRHRPOYXVMEEP-UHFFFAOYSA-N 0.000 description 1
FMHWAAZOTFVMKR-UHFFFAOYSA-N 1-ethyl-4-(2-methylpropyl)benzene Chemical compound CCC1=CC=C(CC(C)C)C=C1 FMHWAAZOTFVMKR-UHFFFAOYSA-N 0.000 description 1
DMZVZANOMJGHKO-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(C(C)C=O)C=C1 DMZVZANOMJGHKO-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GQEFPXSNRRKUHO-UHFFFAOYSA-N 4-methylpent-1-enylbenzene Chemical compound CC(C)CC=CC1=CC=CC=C1 GQEFPXSNRRKUHO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
LFLZOWIFJOBEPN-UHFFFAOYSA-N nitrate, nitrate Chemical compound O[N+]([O-])=O.O[N+]([O-])=O LFLZOWIFJOBEPN-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP2410576A 1989-12-18 1990-12-14 イブプロフエン及びそのアルキルエステルの製造法 Expired - Lifetime JP2909224B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07451563 US4990658B1 (en)	1989-12-18	1989-12-18	Process for preparing ibuprofen and its alkyl esters
US451563		1995-05-26

Publications (2)

Publication Number	Publication Date
JPH03279345A JPH03279345A (ja)	1991-12-10
JP2909224B2 true JP2909224B2 (ja)	1999-06-23

Family

ID=23792726

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2410576A Expired - Lifetime JP2909224B2 (ja)	1989-12-18	1990-12-14	イブプロフエン及びそのアルキルエステルの製造法

Country Status (5)

Country	Link
US (1)	US4990658B1 (fr)
EP (1)	EP0434343B2 (fr)
JP (1)	JP2909224B2 (fr)
CA (1)	CA2031340A1 (fr)
DE (1)	DE69007256T3 (fr)

Families Citing this family (15)

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US5360938A (en) *	1991-08-21	1994-11-01	Union Carbide Chemicals & Plastics Technology Corporation	Asymmetric syntheses
US5315029A (en) *	1993-05-11	1994-05-24	Ethyl Corporation	Process for preparing aryl-substituted aliphatic carboxylic acid esters by carbonylation
US5315027A (en) *	1993-05-11	1994-05-24	Ethyl Corporation	Catalytic process for preparing the alkyl esters of ibuprofen
US5322959A (en) *	1993-05-11	1994-06-21	Ethyl Corporation	Catalytic carboxylation process for preparing aryl-substituted aliphatic carboxylic esters
DK0705245T3 (da)	1993-06-25	2003-04-14	Merrell Pharma Inc	Nye mellemprodukter til fremstilling af antihistaminiske 4-diphenylmethyl/diphenylmethoxy-piperidinforbindelser
US6147216A (en) *	1993-06-25	2000-11-14	Merrell Pharmaceuticals Inc.	Intermediates useful for the preparation of antihistaminic piperidine derivatives
US5315030A (en) *	1993-09-29	1994-05-24	Ethyl Corporation	Catalytic carbonylation of ethers and thioethers
US5536874A (en) *	1994-11-30	1996-07-16	Hoechst Celanese Corporation	Process for preparing arylacetic acid and arylpropionic acid derivatives
US6683094B2 (en)	1998-07-02	2004-01-27	Aventis Pharmaceuticals Inc.	Antihistaminic piperidine derivatives and intermediates for the preparation thereof
US6730791B2 (en)	1998-07-02	2004-05-04	Aventis Pharmaceuticals Inc.	Antihistaminic piperidine derivatives and intermediates for the preparation thereof
US6444844B1 (en) *	2001-03-20	2002-09-03	Council Of Scientific And Industrial Research	Process for the preparation of a carboxylic acid
KR100460567B1 (ko) *	2002-01-07	2004-12-09	진양제약주식회사	이부프로펜 알칸디올 에스테르 및 이를 유효성분으로함유하는 약제학적 조성물
US20070053984A1 (en) *	2005-03-03	2007-03-08	Monique Spann-Wade	Topical gels compositions
US20080317684A1 (en) *	2006-09-06	2008-12-25	Isw Group, Inc.	Topical Compositions
CN102382148B (zh) *	2011-08-02	2014-04-02	海门瑞一医药科技有限公司	双三苯基膦二氯化钯生产工艺

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IT1014957B (it) *	1974-06-11	1977-04-30	Montedison Spa	Processo per la preparazione di acidi carbossilici da alogenuri organici
ES453989A1 (es) *	1976-11-29	1977-11-01	Ferrer Int	Procedimiento de obtencion de esteres del acido 2-(4-isobu- tilfenil)-propionico.
JPS5635659A (en) *	1979-08-31	1981-04-08	Toshiba Corp	Manufacture of rotor core
IT8123391A1 (it) *	1981-08-08	1983-02-08	Montedison Spa	Processo per la preparazione di esteri di acidi arilpropionici otticamente attivi
IT1139455B (it) *	1981-09-21	1986-09-24	Montedison Spa	Processo per la preparazione di acidi alfa-arilpropionici e loro sali alcalini
JPS5995238A (ja) *	1982-11-19	1984-06-01	Mitsubishi Petrochem Co Ltd	フエニル酢酸誘導体の製造法
JPS5995239A (ja) *	1982-11-22	1984-06-01	Mitsubishi Petrochem Co Ltd	α−（６−メトキシ−２−ナフチル）プロピオン酸の製造法
IT1205284B (it) *	1982-12-14	1989-03-15	Montedison Spa	Procedimento per la preparazione di esteri o di sali di acidi aromatici o eteroaromatici
DE3248468A1 (de) *	1982-12-29	1984-07-12	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von carbonsaeurehalogeniden
US4654436A (en) *	1985-09-05	1987-03-31	Eastman Kodak Company	Carbonylation process for the production of aromatic acids or esters
US4668816A (en) *	1985-11-12	1987-05-26	Stauffer Chemical Company	High yield carbonylation of halo-hydrocarbons
US4713484A (en) *	1985-11-12	1987-12-15	Stauffer Chemical Company	Single phase carbonylation of aromatic halides to carboxylic acid salts
CA1338592C (fr) *	1988-04-22	1996-09-10	Varadaraj Elango	Methode de carbonylation d'halogenures arylalkliques

1989
- 1989-12-18 US US07451563 patent/US4990658B1/en not_active Expired - Fee Related
1990
- 1990-12-03 CA CA002031340A patent/CA2031340A1/fr not_active Abandoned
- 1990-12-14 JP JP2410576A patent/JP2909224B2/ja not_active Expired - Lifetime
- 1990-12-17 EP EP90313782A patent/EP0434343B2/fr not_active Expired - Lifetime
- 1990-12-17 DE DE69007256T patent/DE69007256T3/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2031340A1 (fr)	1991-06-19
DE69007256T2 (de)	1994-06-16
EP0434343B1 (fr)	1994-03-09
EP0434343A1 (fr)	1991-06-26
US4990658B1 (en)	1994-08-30
DE69007256D1 (de)	1994-04-14
JPH03279345A (ja)	1991-12-10
DE69007256T3 (de)	2002-06-13
US4990658A (en)	1991-02-05
EP0434343B2 (fr)	2001-09-26

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